


The Art of Letting Him Go

by anotherwinchesterfangirl



Series: Song Prompt Fics [8]
Category: Supernatural
Genre: Angst, Drinking, F/M, Fluff, Oral Sex, Quickie Smut, Slow Dancing, Smut, Weddings
Language: English
Status: Completed
Published: 2016-05-15
Updated: 2016-05-15
Packaged: 2018-06-08 12:43:52
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,553
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6855187
Author URL: https://archiveofourown.org/users/anotherwinchesterfangirl/pseuds/anotherwinchesterfangirl
Summary: <blockquote class="userstuff">
              <p>The reader has an on-again off-again relationship with Dean. She's gotten good at letting him go, even if he does take a piece of her heart each time.</p><p>For the song prompt "So Close" by John McLaughlin.</p>
            </blockquote>





	The Art of Letting Him Go

You’re completely prepared to go by yourself. You are. It sucks that your date cancelled at the last minute, but you’re a big girl. And you can’t miss your cousin’s wedding just because you don’t have a date. That sounds lame as hell, even to you. So you’re fully prepared to attend the wedding stag when Dean unexpectedly shows up on your doorstep.

You’re already in your dress and about halfway through applying your makeup when the doorbell rings. 

“Dean?!” you exclaim as soon as you see his flannel-clad shoulder through the peephole, before you even open the door.

“Whoa, hey,” he says, the words sort of punching out of him as you slam into him and throw your arms around his neck. When you step back, he’s smirking. He notices your dress, his eyes scanning up and down your body. “Wow, aren’t you a sight for sore eyes. You got plans tonight?”

“I do.” Your face falls, but just for a moment. Dean opens his mouth to speak, but you interrupt him. “Actually, I could use a date.”

“A date?” He raises an eyebrow at you, and your knees wobble a little. “A date to where?”

“A wedding,” you mumble. You know it’s not really Dean’s thing. 

“Oh, sweetheart, you don’t want to take me to a wedding.” He gestures to his dirty jeans, worn flannel shirt, and scuffed up boots. 

“Are you kidding me? You’ll be the best looking guy there. And the most fun. You’ve got a suit somewhere, don’t you?” He looks at you skeptically, his eyebrow still raised. “There will be free food.” You’re grasping at straws now, but he still doesn’t look convinced. “Open bar?” That gets his attention. 

“Free booze  _ and _ a pretty girl on my arm? Alright, count me in.” He smiles wide and puts his hands out to his sides, palms up in surrender. You squeal and throw yourself into his arms again. 

“Thank you, Dean,” you say, muffled into his shoulder. He squeezes his arms around you affectionately. 

“When do we leave?”

You step back into the house and glance at the clock on the wall. “Um, a half hour or so? Is that okay?”

“My suit’s in the car.” He smiles. “I’m gonna look like a fed though, just so ya know.” He turns on the heel of his boot and walks back down to where the impala is parked on the curb. You stare, admiring his bowlegged swagger. You wish he could wear those jeans to the wedding. 

 

**

 

You met Dean when you were in college. You and your girlfriends were on a spring break road trip to New Orleans for Mardi Gras, and he was the hottest guy in the bar, almost too gorgeous to be real. Your friends chatted and danced, but you couldn’t stop watching this guy shoot pool, hustling the sucker he was playing for nearly $300, the smug smirk on his lips barely disguised as he sipped his beer. You couldn’t help imagining those lips dragging across your body, and as he met your eyes and quirked an eyebrow at you across the bar, your whole body flushed.

Four shots of tequila later, you reapplied your lipstick and fluffed your hair and sidled up next to him at the bar. 

“Hey there, gorgeous,” he drawled, licking his lips. He flagged down the bartender with a wave of his fingers. “Whatcha drinkin’?” 

“Tequila,” you said, giggling for no reason at all except that he was just  _ so gorgeous  _ and he was looking at  _ you _ . He made you feel like the only girl in the whole place.

You drank for a while, feeling giggly and light, with you doing most of the talking. He didn’t reveal much about himself, just that he was there doing some work for his dad and he was leaving town soon. When you asked him where he was from he said, “Nowhere.” He bought you another drink and a plastic cup of water to go with it—”You’ll thank me in the morning, sweetheart,” he said—and caught you with a hand at the small of your back when you nearly toppled off your stool. His lips brushed your ear. “You wanna get outta here?”

You giggled all the way down the street and into the backseat of his hulking black car, where he spread out a blanket and fucked you slow until you were gasping and shaking and the sun was peeking up over the horizon. 

The two of you spent the rest of the week together, alternately sightseeing and fucking, and when it was time to leave he kissed you hard in the motel parking lot while your friends waited in the car. He pressed a scrap of paper into your hand—“If you ever need anything, call me, alright?”—and then rumbled away in that sexy black car. 

Your heart felt cracked open at the end of that week, but it was just a fling. You knew from the beginning that it was just a fling, so you told yourself to buck up and get over it. You never expected to see him again. You didn’t even know where he was from or what he did for a living or his last name.

And then he’d shown up—the first week of classes the following fall—right at your doorstep (he had a habit of doing that), and you about dropped dead with shock. He could only stay the weekend that time, but it was one of the best weekends of your life. And that’s how it was with you and Dean—he’d show up, you’d spend a few days together fucking and cuddling and laughing, and then he’d be gone again. You fell in love with him a little more every minute you spent with him, but he needed you to let him go, and you knew that. 

  
  


**

 

When Dean walks out of your spare bedroom in his navy blue suit and tie, his hair gelled up at the front and his face freshly shaven, you’re so tempted to ditch the wedding and just drag him into your bed. But he smiles and says, “Alright, let’s do this!” and you really want to show him off. You’re in the stage of your life when everyone in your family is constantly asking you when you will be getting married, and while you know that Dean isn’t about to be the man you settle down with, it will be fun to pretend for an evening. 

Dean is the perfect date—he charms the socks off your mother, makes your uncle laugh so hard he snorts, and even entertains your two year old niece during the ceremony. After a few glasses of wine, you’re warm and happy, leaning on Dean’s shoulder as you watch the happy couple dance their first dance. Afterwards, they open up the dance floor, and Dean turns toward you. 

“You wanna dance, sweetheart?” he asks, his voice low, almost a whisper. Your eyebrows shoot up in surprise. 

“I didn’t really think dancing was your thing?” you say, setting your glass of wine on the table. 

His eyes flick down, glancing over your body and back up to your face. His teeth drag across his bottom lip, and he knocks back the remainder of his beer before he responds. “Well for a girl like you, a guy might just make an exception.” He quirks an eyebrow at you as if to say,  _ Are we doing this or what? _ And you jump up from your seat. 

“I might just have to take you up on that,” you say, pulling him out of his seat by the hand and dragging him behind you to the dance floor. He slides his arms around your waist and hooks his fingers together at the small of your back. You wrap your arms around his neck and rest your chin on his shoulder, following his lead as he sways back and forth to music. You take a deep breath and he tightens his hold on you a little, tucks your head in under his chin. He smells like laundry soap and beer and cheap deodorant, and it reminds you of every time you’ve been together—exchanges of hot breath in the backseat of his car, skin sliding slick together, wet and fluttering, raw and open and vulnerable. Wrapped together in early morning light when everything seems still and sort of timeless, the safe feeling that floods your chest whenever you’re in his arms. How easy it is in that moment, in this moment, to pretend that he’s yours. Your chest aches.

“Thanks for coming with me, Dean,” you murmur into his suit jacket. 

“Are you having a good time?” He leans down to whisper in your ear. 

“Yes, the best time,” you reply, shivering slightly at his hot breath on your neck. He squeezes you tighter, his fingers slipping a little on the satin under his hands. This is how it always is with Dean—you don’t have to say it, he just knows. He knows when to hold you tighter and when to kiss you slower and when to fuck you harder. Suddenly, you don’t want to be here anymore; you want to be naked in your bed with Dean. 

You lean back so you can look up into his face. “You wanna get outta here?” you ask. He smiles slowly.

“I thought you’d never ask.”

 

**

 

You’d never forget the time Dean showed up at your doorstep the year before he went to hell. You didn’t know it then—you didn’t know anything then. But you could tell something was different about him almost instantly. He kissed you hot and hard and desperate, all grasping hands and hot shaking breath, like it was going to be the last time he ever saw you, the last thing he ever did. “Dean... Dean,” you interrupted his kiss, stilled his hands on the clasp of your bra. “Are you okay?”

“What? Yeah. Yes, I’m fine.” He kissed you again. “I just... I don’t have much time.”

“What? What does that mean?” 

“Nothing. It doesn’t mean anything.” And his hands were cupping your breasts, his tongue in your mouth, and you forgot all your questions. 

But afterward, you sat together on the couch and you cried as he told you everything, tears sliding down his own cheeks. And you could barely stand to let him go then. It was like torture, like someone was removing your fingernails one by one, you wanted to reach inside yourself and pull out your heart, you wanted to trade your soul for his so he could live. But he kissed you long and slow on your front porch, leaned his forehead against yours for a moment, and then made his way down the steps and into his car. You tried to memorize every second—the curve of his shoulders under his leather jacket, the thump of his boots on the pavement, the creak of the impala’s driver’s side door, the rumble of her engine. He kept his eyes on the rearview mirror the whole way down the street. You really didn’t think you were ever going to see him again that time. 

But he came back. You’d learned that about Dean in all the years you’d known him—he always comes back. It’s an unspoken pact of your relationship—you let go, he comes back. Over and over and over. 

 

**

 

You barely make it inside the front door before Dean is sliding the zipper of your dress down. He pushes the satin down over your hips and it drops into a puddle at your feet. You fumble at his belt buckle, your fingers heavy from three glasses of wine, and he helps you work it open. He removed his tie as soon as you got in the car, and the top three buttons of his white shirt are hanging open. You surge up on tiptoe, unsteadily swaying into him, and kiss the soft spot just under his jawline, his stubble rough on your lips. You slide your hands down his stomach and into the now open waistband of his pants, fist easy around his cock. You push his pants and boxers down with your other hand.

“Fuck me, Dean,” you whimper, pushing your hips forward and grinding his cock against your damp panties. 

“Jesus, sweetheart,” he rumbles in your ear. His hands are on your ass, and he lifts you against his chest and then leans forward, lowering you onto the stairs. He catches himself with his hands on the stair above your head and kisses your swollen lips, his hips settling between yours, and the pressure of his cock against your throbbing clit makes you moan. 

Dean drags his lips to your ear, your neck, down over your collarbone, your breasts, your stomach. You wiggle out of your panties expectantly, and he pushes your thighs open further, bends your knees up so he can settle between them. 

When his tongue meets your pussy you cry out so loudly you’re sure your neighbors can hear, but you don’t care, and in record time you’re shaking and shuddering, clenching hard around two of his fingers, your breath coming fast and hard. 

“Dean,” you say, still panting. “Dean, I want you inside me  _ now _ .” 

He laughs and wipes your slick from his lips with the back of his hand. “You got it, babe.” 

He fumbles in his pants pocket for a condom, tears it open, and slides it on. Then he’s filling you up so full you can hardly breathe, and you forgot how good he felt, how perfectly you fit together. He bends his head down over your shoulder, breathing heavy against your skin as he pumps into you, fast and hard, the angle of the stairs keeping you close, so close your breasts are pushed up against his chest and his pelvic bone grinds against your clit with every thrust. 

“Oh my god, Dean,” you cry, already on the edge of your second orgasm. “ _ Dean _ ,” you cry as you let yourself tumble over the edge, squeezing your arms around his broad back. He lasts a few more thrusts before he pushes in deep, drags himself up against you, and comes with a shout and a curse, forehead pressed against your shoulder. 

“We didn’t even make it to the bed,” you say with a giggle. He pulls out and rolls to the side, props himself up with an elbow on the stair, and looks down at you grinning. 

“Oh, we’ve got plenty of time for that.” 

 

**

 

Two days later, you stand on your porch in pajamas and socked feet, trying not to cry as he says goodbye, again. You should be used to this by now, dammit, you’re a professional at saying goodbye to Dean Winchester. He kisses you soft and slow. 

“Call if you need anything, okay? If anything weird happens.”

“I know.” You try to smile, but the corners of your lips wobble. 

“I’m sorry I can’t stay,” he says low, wiping a tear from the corner of your eye with his thumb. You nod, closing your eyes briefly. 

“I know,” you say again. “Be safe out there.” He nods. “Goodbye, Dean.”

“See you soon, sweetheart.”

And you let him go. 

 

**Author's Note:**

> Feedback is SO appreciated! Thanks for reading!


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